☕️ (R)emote Expresso #43

Hi (R)emotes,

☕️ (R)emote Expresso is your weekly dose of creator insights on remote collaboration designed to fuel your day, delivered once a week in your inbox 💌

Hey Remote Rebels and Digital Daydreamers,

Remember the “hallway question”? That magical moment when you could just lean over and ask someone, “Hey, where’s the latest version of that thing?” 

Yeah… remote work sent that moment to live in the same graveyard as office birthday sheet cakes.

Now, information hides in half-finished Google Docs, someone’s private Notion page, or a file named “Draft_v3_FINAL(2).xlsx.” 

New hires? They’re basically dropped into a corporate escape room.

Veterans? Answering the same question so often they deserve a loyalty punch card.

And this isn’t merely a nuisance. McKinsey says we spend 20% of our workweek hunting for information. That’s one full day every week playing digital hide-and-seek instead of, you know… actually working.

🎭 How Each Generation Feels It

• Gen Z: Starts a new job and gets told, “It’s all in the wiki.” The wiki? Last updated before they were in college.

• Millennials: Trapped between Slack pings and Confluence rabbit holes, dreaming of the one clean SOP that never existed.

• Gen X: Remember when everything was in a binder? Not better, but at least you knew where the binder was.

• Boomers: Knowledge-sharing = mentorship. Remote makes that harder, and they miss the pass-down moments.

Different flavors of lost. Same scavenger hunt.

🌐 Why This Belongs in (R) Generation

Connection isn’t only about people - it’s about ideas. And when those ideas get trapped in private folders or someone’s brain, everyone pays the price.

New teammates waste weeks chasing ghosts in Google Drive. Leaders repeat themselves until their calendar groans. Whole teams lose trust when the “answer” depends on who you know, not what’s documented.

That’s not just inefficiency. That’s disconnection. It’s the slow leak that drains creativity, collaboration, and confidence.

But here’s the hope: we can do this differently. Remote work doesn’t have to mean knowledge-hoarding dragons and “Final_v3” graveyards. It can mean a culture where sharing is easy, documentation is a gift, and information flows as freely as ideas.

That’s how remote work stops feeling like a scavenger hunt - and starts sounding like a symphony.

If we want remote work to thrive, we’ve got to stop guarding knowledge like dragons and start building cultures where ideas actually flow. And speaking of flow - the next (R) Generation event is all about unlocking new ways to collaborate and innovate, this time with AI as your sidekick.

🧞 Your Design Thinking Sidekicks

Hosted by Kusuma Sukma | Learnly Society | 60 minutes

🗓️ Wednesday, Sept 24 | Beginner-friendly

3 AM CDT | 9 AM WEST | 10 AM CEST | 1:30 PM IST | 6 PM AEST

What if your next big idea didn’t have to come from you alone? In this playful workshop, you’ll discover how AI can be your brainstorming buddy, your creative co-pilot, and even your secret weapon for innovation.

Using the Design Thinking framework, Kusuma will show you how to “talk” to AI like a pro, co-create ideas in Miro, and turn creative chaos into actual solutions. Whether you’re new to AI or just ready to shake up your process, you’ll leave with tools to future-proof your career - and maybe even a few wild ideas you didn’t see coming.

💡 Expect hands-on co-creation, zero coding, and a lot of “aha!” moments.

🧩 Fixes for Knowledge Hoarding

1. Document like your future self is a goldfish. Assume zero memory.

2. Rotate “librarian duty.” Once a week, someone updates and curates the knowledge base.

3. Make it findable. If Slack search is your primary archive, you’re doing archaeology, not knowledge-sharing.

4. Reward oversharing. Not just vacation selfies - actual know-how.

5. Design for handoffs. Build processes where information automatically passes along, instead of being guarded like treasure.

None of these shifts require wizardry - just a little consistency and care. But the truth is, the best way to fix information gridlock might be something we haven’t even named yet. That’s where your AI sidekick comes in.

🪄 AI prompt to try:

“I work remotely and often struggle with knowledge hoarding or missing documentation on my team. Suggest 10 unconventional strategies (beyond the usual wikis, SOPs, or Slack channels) to make information easier to find and share. Make them: 1) grounded in research on knowledge management or collaboration, 2) playful and energizing so people actually want to do them, and 3) realistic for a team that includes [insert: new hires, managers, introverts, night owls, etc.]. Include at least one strategy that feels delightfully weird but still possible.”

🪄 Your Turn

We’ve all been there - trapped in the corporate scavenger hunt, digging through Final_v2 files and praying to the Slack gods. Let’s swap stories (and maybe some survival hacks).

👉 Spill it: What’s the weirdest place you’ve ever found the info you needed? (Bonus points if it was someone’s brain 🧠).

👉 Or confess: are you the secret dragon guarding the team’s precious Confluence logins? 🐉

Hit reply and drop your tale - the juiciest ones may just make it into a future Espresso.

Still sticking Post-Its to my goldfish,

— The (R) Generation Team 🧡

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BE A PART OF
THE R GENERATION COMMUNITY

R GENERATION brings together remote professionals from 50+ countries to explore the future of work through events, workshops, and AI-powered collaboration. Join a community where curiosity meets innovation and connections transcend borders.

Less grind, more grin 😏